Contrast media for x-ray photography



Patented July 26, 1932 UNITED STATES PATENT OFFICE GERHARD HECHT, 0FWUPPERTAL-ELIBERFELD, ANTON O SSENBECK, OF COLOGNE- MULHEIM, AND ERNSTTIETZE, OF COLOGNE, GERMANY, ASSIGNORS TO WINTHROP CHEMICAL COMPANY,INC., OF NEW YORK, N. Y., A CORPORATION OF NEW YORK CONTRAST MEDIA FORX-RAY PHOTOGRAPHY No Drawing. Application filed December 31, 1931,Serial No. 584,272, and in Germany July 8, 1980.

The present invention relates to new contrast media for X-rayphotography.

It is known that compounds containing iodine are in some cases proved tobe suitable for use as contrast agents, which are of importance in theX-ray photography of organs, particularly also of the urinary passages.However, the contrast agents employed up to date in the medicinalpractice require the use of relatively great volumes of the solution ofthe contrast agent owing to an insuflicient iodine content of the agentsused. Therefore, efforts are being made for raising the iodineconcentration to obtain a deepening of the X-ray shadow.

In accordance with the present invention water-soluble salts ofdiiodo-methane-sulfonic acids of the probable general formula:

wherein R stands for hydrogen or an alkyl group, are to be used ascontrast agents in order to produce an X-ray shadow in the organs filledup with these media. The watersoluble salts of thediiodo-methane-sulfonic.

acid and its homologues are distinguished by a very high iodine contentand by a good solubility in water.

The new contrast media may be introduced Sometimes it is also possibleto employ the contrast agents per os. We prefer to use the alkali metalsalts of the diiodo-methane sulfonic acid or its homologues, such asmethylethylpropyland isopropyl-diiodo-methane sulfonic acid. Also someamine salts are of particular value for the use of the said acids ascontrast agents, for example, the diethylamine salts, thediethylaminoethanol and ethylenediamine salts, which are likewisereadily soluble in water.

The salts of diiodo-methane-sulfonic acid and alkyl substitutionproducts thereof, are prepared by reacting upon an alpha-halogen aceticacid or an alkyl substitution product thereof with a neutral sulfite andiodizing the sulfo-acetic acid or the alkyl substitution product thereofobtained at a high temperature by means of iodine. Thereby carbondioxide is split off and two iodine atoms are attached to the carbonatom substituted by the sulfonic acid group. The preparation of thediiodomethane sulfonic acid according to the above directions has beendescribed by Backer, Receuil des Travaux Chimiques des Pays Has, 45,page 833.

The invention is further illustrated by the following examples withoutbeing restricted thereto E wample 1 A 20% solution oflithium-diiodo-methane sulfonate is injected by means of catheterizationof the ureter into the pelvis of the kidneys. A few minutes later theX-ray photograph is taken in the usual manner.

Ewample 2 5 grams of sodium-diiodo-methane sulfonate are dissolved in10-20 ccs. of water. The solution is injected intravaneously. Within15-30 minutes in the case of disorders of the kidney function also stilllater an X-ray photograph of the urinary passages may be taken in theusual manner.

'E'wample 3 Into a blood vessel 9.- suitable quantity of an aqueous.20-40% solution of sodiummethyl-diiodo-methane sulfonate is injected inaccordance with the technique customary in vasography. When takingthereafter an raphy, containing a diethylamine salt of an X-rayphotograph the v essel parts being in acid of the probable formula:question are rendered visible.

Emflmple wherein R stands for hydrogen or an alkyl Fistulae are filledup with a suitable quangroup. tity of a 20% aqueous solution of sodium-9. Contrast medium for X-ray photogdiiodo-methane sulfonate. On an X-rayraphy, containing the diethylamine salt of photograph the position andextension of the diiodo-methane sulfonic acid. canal of the fistulae isrendered visible. In testimony whereof, we afiix our signatures.

\ GERHARD HECHT.

ANTON OSSENBECK. ERNST TIETZE.

Example 5 A joint cavity is filled up with an about 20% aqueous solutionof diethylamine-diiodomethane-sulfonate and an X-ray photograph is takenin the customary manner.

Example 6 A maxillary sinus is rendered visible for X-ray photography byinjecting a suitable quantity of an about 20% aqueous solution ofdiiodo-ethane sulfonic acid sodium.

Example 7 wherein It stands for hydrogen or an alkyl oup. 2. Contrastmedium for X-ray photography, containing an alkali metal salt of an acidof the probable formula:

wherein R stands for hydrogen or an alkyl oup. 3. Contrast medium forX-ray photography, containing a water-soluble salt of diiodo-methanesulfonic acid.

4. Contrast medium for 'X-I' ay photography, containing an alkali metalsalt of diiodo-methane sulfonic acid.

5. Contrast medium for X-ray photography, containingsodium-diiodo-methane sulfonate.

6. Contrast medium for X-ray photography, containing an amine salt of anacid of the probable formula:

wherein R stands for hydrogen or an alkyl group.

7. Contrast medium for X-ray photography, containing an amine salt ofdiiodomethane sulfonic acid.

8. Contrast medium for X-ray photog- Hill

